Medicare Enrollment Specialist — Clinical AI Evaluation (Remote AI Evaluation Contract)

Join Jobtacular as a remote Medicare Enrollment Specialist — Clinical AI Evaluation (Remote AI Evaluation Contract) ($40 - $60/hour). We partner with leading AI research laboratories across major English-speaking markets to evaluate complex responses, design realistic domain scenarios, and calibrate next-generation foundation models using deep professional expertise in Medicare, Enrollment, Coordination, Coverage.

What You Will Do

• Write rubrics that define a correct, complete answer on initial enrollment, special enrollment periods, and Part B late penalties, including how enrollment ties to Social Security benefits.
• Cover Medigap vs. Medicare Advantage and Part D in your rubrics, with a focus on scenarios involving employer or retiree coverage.
• Cover how employer coverage interacts with Medicare, including employer size, primary vs. secondary coverage, COBRA, and creditable coverage.
• Assess and benchmark model-generated answers against your rubrics, flagging errors, omissions, and common misconceptions.
• Share clear written feedback with the project team, working asynchronously.
• Former SSA Medicare enrollment experience, or employer benefits/HR experience advising employees on Medicare
• 1+ years advising on initial enrollment, special enrollment periods, Part B late penalties, Medigap vs. Medicare Advantage, and Part D

Who We Are Looking For

• Practical background using premium adjustments (such as IRMAA), working while enrolled, or HSA rules alongside Medicare
• Experience creating guides, counseling scripts, or training materials
• Experience helping a diverse range of beneficiaries, including rural and non-English-speaking clients
• Compensation Band: $40 - $60/hour
• Work Location: Remote (100% Remote / Asynchronous Flexibility)
• Available Openings: 10 open positions
• Core Competencies: Medicare, Enrollment, Coordination, Coverage, COBRA

Compensation & Remote Structure

• Compensation Rate: $40 - $60/hour (contract specialist remuneration)
• Work Arrangement: 100% Remote / Work From Home
• Eligible Remote Countries: United States, United Kingdom, Canada, Australia, New Zealand, Ireland, and South Africa
• Core Competencies: Medicare, Enrollment, Coordination, Coverage, COBRA
• Hiring Agency: Jobtacular

Direct Application Process: Click the Apply button on this page to proceed directly to our partner application portal and submit your profile for immediate consideration.